Nothing is known of James Caldwell’s origins, date of arrival in the province of Quebec, or beginnings in business, but by 1784 he was established in Montreal, where he signed the petition seeking an assembly for the province. Three years later he was listed as a lieutenant in the British Militia of the Town and Banlieu of Montreal. In October 1790 he joined other Montreal merchants in requesting Governor Lord Dorchester [Guy Carleton] to create a custom-house in Montreal to reduce the costs, losses, and delays caused by the fact that there was only one office, located in Quebec. Caldwell was dealing in wine, beer, various foodstuffs, hardware, and other goods. In 1793 and 1794 he exported wines to Upper Canada and the Great Lakes region.

Being a shrewd businessman, Caldwell no doubt had his mind set on picking up a share of the lands being granted by the government in the new Lower Canadian townships. From 1792 to 1812 he, along with partners such as Alexander Auldjo*, submitted a constant stream of petitions. In accordance with the system of township leaders and associates in effect until about 1809, an applicant, having first secured the support of the Executive Council, senior officials, and governor, would recruit some associates to sign his application for a land grant; as soon as the letters patent were issued, the associates, who ordinarily received 1,200 acres each, would transfer all but 200 acres to the leader for a nominal sum. In 1802 Caldwell took part in the allocation of half of Aston Township, and in 1806 he received letters patent for 1,853 acres for himself, his wife Louisa Melvin, and their three children, Alexander, Louisa, and Amelia (Mary).

Caldwell seems to have maintained excellent relations with the powerful class of businessmen and ubiquitous officials, and this practice probably helps account for the numerous government appointments he received. Along with Auldjo and François Desrivières, in 1805 he became a warden in Montreal of Trinity House of Quebec, which at the urging of John Young had been founded that year by the assembly. In addition to holding that honourable and lucrative post, he was made a commissioner for the improvement of inland navigation between Lachine and Montreal in the same year, and then in 1806 a justice of the peace. Early in 1810, when Stephen Sewell*’s election to the assembly for Huntingdon was contested, Caldwell served as one of the commissioners to hear the witnesses for both sides. His duties as a magistrate were increased in 1812 by a commission authorizing him to receive the oath of allegiance. The following year, when the Act for the Relief of Insane Persons and for the Support of Foundlings came into effect, he was again made a commissioner, in company with Desrivières. In 1814, having declined appointment as a returning officer, Caldwell accepted a commission to oversee the removal of the old walls and fortifications of Montreal, and also became a commissioner for the building and repair of churches.

While attending to his commercial activities, which he had not given up, and to his administrative duties, Caldwell had steadily risen in the ranks of the local militia, becoming captain in 1797, major in 1811, and lieutenant-colonel of the 1st Battalion in 1813. He was also interested in the arts and letters and accumulated a collection of books, maps, and engravings. In this respect he seems to have been fairly typical of certain businessmen of the time, such as his friends James McGill, Joseph Frobisher, and William McGillivray* who, ready to take any opportunity to increase their wealth, also extended their influence to charitable, educational, or cultural works, thus assuring their social advancement.

Worn out by a long and painful illness, James Caldwell died on 18 April 1815. His funeral was conducted by the Reverend Jehosaphat Mountain, minister of Christ Church, where he had owned a pew.

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